375th time's the charm Or not
by nocloudypooh
Summary: After Gary failed to ask Leaf out for the 374th time, Ash suggests Love Potions to remedy the situation. Of course, it turns out to be a disaster, and Gary should have known better than to let Ash come up with the idea, or have him in charge of the plan. One-shot, set in the magical world of Harry Potter. Leafgreenshipping (Leaf x Gary).


**Brief note: This story places the Pokemon characters within the magical world of Harry Potter, and does not involve any of the Harry Potter characters. Only relevant parts of the magical world is mentioned, as I did not want to included too much details of the cross-over world in a one-shot. You can ask me any questions about the setting if you are confused through the reviews or PM! Also I do not own anything related to Pokemon or Harry Potter.**

 _Italics refers to character's thoughts._

xxx refers to section breaks.

 **Summary: In which Gary tries to get Leaf to go out with him with the help of his friends. Of course, it turns out to be a disaster, and he should have known better than to let Ash come up with the idea, and have him in charge of the plan.**

* * *

 **375th time's the charm. Or not.**

The day has barely begun and Gary slumped down at the table in the Great Hall with a loud thud, earning looks from his housemates sitting near him.

"What's wrong, Gary?" his best friend and fellow housemate Ash asked as he helped himself to more servings of bacon and scrambled eggs.

"I'm an absolute failure," came a muffled response. "Whyyyy?"

"Is this about Leaf again?" Paul asked from across the table.

"I don't get ittt," moaned Gary, "why won't she just go out with me already?"

Mouth still full of food, Ash patted his friend sympathetically on the shoulder. It's no secret to the whole school that Gary Oak has been trying to ask Leaf Green aka the-girl-with-the-brains out for years. And even more people know that the girl has never failed to hex him with a different curse each time he tried to ask her out.

"So what did she hex you with this time?" Drew asked from beside Paul, helping himself to some toast. The girl's knowledge of hexes surpasses just about everyone, and Drew learns most of his curses from what she used on Gary.

Gary straightened himself and turned to give Drew a glare. "That's beside the point," he emphasised. "I don't understand why Leaf still doesn't want to go out with me! I'm just about the most eligible bachelor in this entire school!" he continued, hands gesturing wildly around the Great Hall.

His three friends merely look at him with raised eyebrows, and burst into collective laughter. "It's not funny guys!" Gary protested indignantly. "This is like the hundredth time she rejected me!"

"Three hundred and seventy-fourth time actually," Paul corrected, causing Ash and Drew to erupt in laughter once more and Gary to sputter incoherently.

"Class starts in 15 minutes, we better head off soon or we'll be late. Let's go, Paul." Drew stated as he wipe tears of laughter from his eyes. Gary groaned, and slumped down once again on the table. "The whole world hates me," he declared.

Ash could only smile and shake his head, helping himself to more food before he heads off for class too.

xxx

Potions was as difficult as ever, as Professor Sycamore had set them the task of brewing the difficult Hyper Potion. As usual, Ash struggled through the potions brewing process, barely scraping a pass for his potions grade at the end of the class.

Once everyone had submitted their vial of potions, Sycamore launched into a whole speech on how they should prepare for their O.W.L.s, which Ash immediately tuned out of.

"... All of you should take a leaf out of Miss Green's book, who have displayed excellent result based on her love of potions! O.W.L.s are important at this stage in your life ..."

 _Love.. potion?_ Ash thought drowsily. Just like that, an idea popped into his head and he can't wait to tell Gary at lunch.

xxx

"A Love Potion?" Drew asked incredulously, once he heard Ash's plan.

Ash nodded eagerly. "This way, Leaf will have to fall in love with Gary for sure!"

"This is stupid," Paul stated, wondering how Ash even came up with this idea.

"I don't know.." Gary pondered, "it sounds like it might actually work.."

"It will, trust me," Ash assured Gary.

"Well, if you say so then I'm in!" Gary announced, looking at Drew and Paul for support.

Drew and Paul shared a glance before sighing silently. There's no changing their friends' idiotic mind now that they have set their mind to it. Better join and try to minimise the damage. "We're in too."

"Excellent," Ash said as he clapped his hands together. "Now time to put the plan into motion."

xxx

For once, Ash feels very proud of himself for coming up with a plan that all his friends agreed with. It's a simple plan, but one wrong step will spoil everything and potentially end up with them in detention for the rest of the school year. Ash shuddered at the thought, remembering the rumours of the pikachu detentions that spread through the school like wildfire. _No, this needs to be foolproof and I know just the thing to do._

Just then, he caught sight of a bob of orange hair turning into the corridor. _Alright, time to put the plan into action!_

"Misty! Hey Misty! Wait up!"

Said orange-haired girl paused at the sound of the name, and turned to see Ash running towards her from the end of the corridor.

"What is it, Ketchum?" she asked coolly. While they were all acquainted, Misty never felt the need to refer to the boys with their first name. Which was odd, seeing that they boys never have an issue with using the girls' first name.

"It's about Gary and Leaf. I'm sure you heard that Leaf rejected Gary again this morning?" he inquired.

Misty raised an eyebrow. "I was there when it happened. So?"

"Well I have this plan to get them both together!"

xxx

"A Love Potion?" Dawn asked, eyes shining with excitement.

After Ash had convinced Misty of his plan (how, Misty would not say, but her cheeks turned pink at the question), Misty had wasted no time in conveying the plan to the girls, with the exception of Leaf of course. Knowing Dawn and May as the hopeless romantic they are, Misty doesn't have a doubt that they will agree to the plan.

"Ooh I can't wait for Leaf to fall in love with Gary after she drinks the potion!" May exclaimed, giggling alongside Dawn.

"We'll have to wait for the potions to arrive. The boys ordered some from the famous joke shop and the order will take about a week. Then it will be up to us to slip the potion to Leaf without her knowing," Misty explained patiently, though she is as excited as the other two girls of the plan. While Leaf is one of the most eligible girl in the school, she has never paid any interest to any boys, choosing instead to focus on her studies. Dawn and May have long since given up on setting up blind dates for Leaf at Hogsmeade, and the boys in school have given up on trying to woo the affections of the girl. With the sole exception of Gary of course, which annoyed Leaf to no end. But Dawn, Misty and May all secretly hope that Leaf will fall in love soon, and start having a love life besides all her school work.

"I can't wait for it to happen!" Dawn gushed, her eyes glazed over as she imagined the scene in her head.

"Don't we all," agreed Misty. "Now we have to make sure that Leaf never finds out about this. We don't want to be on the receiving end of her hexes."

"Of course!" chimed May and Dawn.

xxx

At long last, the boys received their order of Love Potions by owl mail, disguised as regular drinks to avoid confiscation by the caretaker. As they did not have any classes on Saturday, the boys and girls except for Leaf met up at a secluded corner of the school to discuss the plan once more and to set the next step in motion.

"Alright, we have charmed the Love Potions such that whoever drank it will start to fall in love with Gary. The instructions say that each vial of potions will last for a day, so the dozen vials we ordered will last us for twelve days. It says here that at the end of these twelve vials, the drinker would have fall so deeply in love that the potion would not be needed to sustain it any longer. It's up to you girls to make sure that Leaf drinks a vial of this every day then," Ash rattled off the instructions he memorised as he handed the potions over to the girls.

The girls nodded determinedly, already having an idea of how they would slip the potion to Leaf.

"Alright, we will give the signal to Gary once Leaf has drank the potion and he can work his magic on her," Misty said, as May and Dawn nodded beside her.

"Great! Thank you girls for your help, I'll be sure to invite you three to our wedding if everything goes according to plan," Gary said cockily.

"The Love Potion does not have guaranteed results," interjected Paul, "it's only supposed to help the drinker fall in love easier with a specific person. If it doesn't work by the end of it all, then Gary should just give up on Leaf."

"Oh don't be such a spoilsport, it's going to work for sure." Dawn waved him off, earning a glare from the purple hair boy.

"Don't forget to keep all this from Leaf as well, even if the plan were to fail," Drew interjected before Paul could retort Dawn's comment. "We all know how good she is with her wand."

"Break it off guys," Gary said sharply, as May looked like she is about to retort to Drew's comment as well. "I'm sure the girls know what to do." _Honestly, when will they stop arguing and start going out already_ , thought Gary as he shook his head mentally. It's so obvious to him that Drew and May as well as Paul and Dawn are going to get married at the rate they snap at each other.

"Alright, let's go and put this plan into motion!"

xxx

"Leaf!"

The brunette heard her name and spun around, spotting her three best friends running towards her.

"There you guys are! I woke up and didn't see you three in the dormitory! So I came down and didn't see you at the Great Hall either! Where have you been?" asked Leaf, as they looked for seats at the long tables.

"We were at the library," lied Dawn flawlessly, "working on that essay for Professor Elm. You know we are not as good as you when it comes to keeping up with our school work, Leaf."

Leaf nodded, believing in their made-up story, and not noticing the small breath of relief that Misty and May let out. "Well come on or all the food will be gone before we get the chance to eat it!"

The girls sat down and hungrily ate their breakfast, while the boys watched them from the other side of the Great Hall.

"May! You ate so much that all the food in front of us is gone! Again!" complained Misty. "And I'm not even done with breakfast yet."

May grinned sheepishly and continue eating the massive amount of food that she has piled onto her plate. "You know my appetite, Misty."

"It's alright, Misty" soothed Leaf. "I'll go get us more food from further down the table." With that, the brunette turned her back on her friends and went to get more food from the rest of the table.

"Quick! Pour the potion into her pumpkin juice now!" hissed Dawn as she kept an eye on Leaf to make sure that she doesn't turn around and spot them doing anything.

Hastily, Misty uncorked one vial and poured the entire contents into Leaf's goblet, and hide the empty vial inside her robes just as quickly.

"Pretend nothing happened," hissed Dawn as she spotted Leaf coming back with plates of food.

"Thanks Leaf, you are such a dear," Misty smiled sweetly at Leaf when she placed the food in front of the girls.

"You're welcome," Leaf replied with a roll of her eyes, and reached out to her goblet for a drink. All three girls (and four boys from afar) eyed her closely as she take her drink, anticipating something to happen. To their disappointment, Leaf merely took a small sip before setting her goblet back down again.

Feeling a tiny nudge from her side, Dawn tried to remedy the situation immediately. Reaching for her own goblet, she commented loudly, "You know girls, the weather has been getting pretty warm lately, we ought to drink more to replenish all the moisture we lost in the day! We wouldn't want our skin to become parched and dry!"

Playing along, May took her own goblet as well and added,"Pfft I don't know anything about parched and dry skin, but I know for sure that we will fall sick if we don't drink enough water!"

"I say we should down all our goblet right now for our upcoming O.W.L.s instead!" declared Misty as she raised her goblet in the air.

Laughing slightly at her friends, Leaf lazily lifted her goblet and downed her goblet along with her friends. _Success!,_ the seven boys and girls thought. Seeing that Leaf has finally finished her drink (along with the vial of Love Potion), May proceeded to give the signal to the boys. "Alright," May said as she stretched her arms out wide, "I'm done with breakfast. Going to head to the library to continue on my homework now." She shot the boys an inconspicuous look and the barest of nod, before walking briskly away from the Great Hall.

"So how do you feel, Leaf?" asked Dawn curiously.

Leaf doesn't respond, and her eyes have a glazed look to them that didn't exist just a minute ago. Seeing this, Misty and Dawn got a little worried and tried to get her to respond again.

"Leaf? Leaf, can you hear us?" Misty asked with a raised voice.

"I can't stop thinking about him," she mumbled dreamily in response.

Misty and Dawn exchanged a look, and frantically waved to the boys to come over quicker. The boys quicken their strides and were standing behind Leaf in just a while.

"Leaf?" Gary asked gently, trying to catch her attention. At the sound of the auburn-hair boy, Leaf's head immediately shot upwards and her eyes widened in surprise. "Gary!" she practically screamed, jumping up from her seat and leaping to hug him. "Where have you been! I waited so long for you! I don't know why I kept rejecting you but yes! The answer is yes! Let's go out together!"

Gary's eyes widen in response, surprised that the potion has worked so well and so quickly, before morphing back to his characteristic arrogant smirk. "It's alright Leafy, better than late than never. Let's go now, shall we?" Without backwards glance, Leaf followed Gary out of the Great Hall, while Gary gave a thumbs up to Ash.

"Well that went well," Drew commented as the watch the newly formed couple head out.

"She didn't even say bye to us," said a shocked Dawn. Then suddenly, she erupted into squeals and giggles with Misty as they gushed over the massive progress Leaf has made in her love life. "Oh I'm so happy for her!" squealed Dawn. She was so excited that she didn't even pay any attention to the insult that Paul shot her way ("Troublesome"), choosing to continue the topic of planning Leaf's wedding.

"Well good job Ashy boy," Drew said. "Your plan worked fantastically. Now we just need to see how things goes for the next week or so."

Ash grinned widely and felt a hint of pride. _Problem solved._

xxx

(Two days later, in the common room.)

"Has anyone seen Gary the today?" Ash asked as he put away Professor's Birch homework on Care of Pokemon. "He hasn't even turned up for classes today."

"No," Paul replied in a monotone, not even looking up from his pile of work.

"Probably busy somewhere with Leaf," smirked Drew as he practiced his wand work.

"I wouldn't be surprised," giggled Dawn. "They were practically inseparable for the past few days.I even heard rumours that they were snogging out in the courtyard yesterday."

"Leaf must be so smitten with Gary now," May smirked, as the other girls nod in agreement. "She didn't even do any studying during the weekends."

"Well I hope Gary doesn't do anything wrongful to Leaf," Misty commented matter-of-factly. "If he does he would have to answer to my wand AND mallet."

"Don't worry Misty," assured Ash, "Gary's a real gentleman. He wouldn't do anything to Leaf."

Misty only nodded, and continued working on her essay. The Professors have all set them so much homework in preparation for their O.W. L.s that they are all struggling to keep afloat from their workload.

Just then, the portrait hole to the common room burst open, revealing a panting, disheveled looking Gary. The gang (girls and boys) stared at him in surprise, wondering what on earth happened to the spiky-haired teen.

"Must... Get... Away..." panted Gary, as he tried to catch his breath. Startled by his sudden appearance, the gang approached him hoping to hear an explanation.

"What happened?" Drew asked. "And ew is that lipstick on your face?" He continued, half amused and half disgusted.

"Huh but Leaf doesn't wear lipstick?" Dawn pointed out, bewildered.

"Alright what the hell did you do now, Oak?!" demanded Misty, her face turning into a shade of furious red.

Before Gary could reply any of them however, the portrait hole burst open once more with a voice shouting "Gare Bear~!"

Everyone turned their head towards the portrait hole and gaped at Leaf as she pranced across the common room, face covered in make-up for what must be the first time in her life. "There you are Gare Bear!" she giggled, as she pulled a struggling Gary into a tight hug. "I won~ that's one hundred and seventeen to me and zero for you!" Leaf sang in a completely un-Leaf-like manner.

"..."

"You have got to be kidding me," Paul deadpanned, putting his hand on his forehead.

"Gare... Bear?" Drew repeated, confusion evident on his face.

"Let me go," came Gary's strained voice as he tried to speak while the air is being squeezed out of his lungs.

"Hehehe, you're funny, Gare Bear," Leaf giggled, before proceeding to hug Gary even tighter, "why would I want to let you go now that I have you?"

The gang watched open mouthed at the scene before them, stunned in place as they tried to make sense of the situation. What happened in the few hours they didn't see Leaf and Gary?

"Guys, a li- li- little help please.. dy- dying here," choked Gary from within Leaf's embrace. That seemed to break them out of their trance, and the six teens proceeded to separate Leaf and Gary. Or more accurately, tried to, because Leaf refused to budge and continue holding on to Gary. With great difficulty, the gang separated the two as Leaf shouted "Traitors!", "Gary stealers!" or "Gare Bearrr!" at her friends.

"What happened?" May demanded once the three boys managed to restrained Leaf, ignoring Leaf's cries for Gary.

"I don't know!" replied a distressed Gary. "We were progressing so well these few days but things just started going downhill after she drank her potion today and she got clingy so suddenly. I can't even get out of her sight for a second!"

The gang blinked at the new information. "So... what's this one hundred and seventeen to Leaf and zero to you thing?" Ash asked.

Gary sighed, running his hand through his hair. "I was trying to get away from her, and she thought we were going to play hide and seek. I was practically running through the whole school today until I ran back here. I'm telling you, that girl is one serious seeker and it doesn't help that she is so good with her wand."

"Gare Bear is MINE!" screamed Leaf, as she continue struggling against the hold of the boys.

"Is that how you got all those kisses?" Dawn asked, hugging her stomach as she laughed uncontrollably, unable to hold it in any longer. Despite the situation, the girls have been trying hard to stifle their laughter at the story and Leaf's outbursts and declarations of love for Gary. They know they probably shouldn't have but it's a momentous occasion when Leaf, of all people, is acting in such manner that she wouldn't have if not for the Love Potion.

"It's not funny!" Gary protested. "This isn't supposed to happen! I don't even know what to do with Leaf anymore! It's like she's overdosed on Love Potion or something!"

At that statement, everyone stilled, thinking through the possibility. Which isn't helped by Leaf's demands for "Kissy time, Gare Bear! We haven't kissed for 5 minutes!" or "I want Gare Bear NOW!".

Shaking his head, Drew turned to look suspiciously at Ash. "Say, Ash, do you still have that instructions for the Love Potion?"

"Of course!" he replied, pulling out the instructions sheet. "It's as I said, to give one vial of Love Potion to the drinker everyda-" he stopped suddenly, eyes wide at the piece of parchment.

"Give me that!" Misty snapped, eyes narrowing at Ash. She quickly scanned through the parchment, eyes bulging at what she saw. "Oh you idiot Ketchum!" she screamed. "Look what you've done now!" she fumed, chasing after Ash who at least had the sense to run away.

"No Misty, I swear it was an accident! Misty!" Ash shouted, as the two chased rounds around the common room, to the slight amusement of the rest of the gang.

Curiously, Dawn picked up the parchment Misty drew on the floor and begin reading out loud to the rest of the gang. "For maximal effectiveness of the Love Potions, the drinker should drink the dosage continuously until all twelves vials are finished. Each vial last for a period of one month, and at the end of these twelve vials, the drinker would have fell so deeply in love that the potion would not be needed to sustain it any longer." She gulped and continued. "Caution: Drinking the next vial of Love Potion before the dosage is over will result in over dosage, displayed through symptoms of excessive love, possessiveness and strong desire for physical closeness."

The gang was silent for a moment as they took in the new information, before Gary smacked his hand on his forehead in a face palm. "I should have know better than to let Ash take charge of the plan."

"What now?" May inquired, as they all looked at Leaf, who was still screaming for Gary, displaying the said symptoms of Love Potion over-dosage: excessive love, possessiveness and strong desire for physical closeness.

xxx

"I WAS WHAT?!" Leaf exclaimed from her bed in the Hospital Wing. The gang flinched visibly from her outburst, though it was Gary whose ears hurt the most since he was standing closest to her.

Unable to remedy the situation themselves, the gang had to bring Leaf to Headmaster Oak and explained their current situation. Professor Oak had not been pleased at all, giving them the dreaded Pikachu detention, though he did summon Professor Sycamore to whip up the Love Potion antidote for Leaf.

Slightly annoyed that they got detentions, the gang had "volunteered" Gary to explain the situation to Leaf through a mixture of threats and violence. Hence, Gary stood before Leaf's bed gulping nervously as he tried to delay his inevitable death by Leaf's hands.

"Uh we er fed you some Lo- Love Potion and and uh gave you an overdosage by accident.." stuttered Gary, as the rest of the gang stood a far distance away from the bed. Inwardly however, he is cursing his friends for abandoning him in such a life or death situation to save their own skin.

"And what did I do?" Leaf asked in a dangerously calm voice. Fear gripped Gary at the tone, but Leaf's eyes were glinting furiously at him, daring him to run away, so he has no choice to answer her and pray that Arceus will have mercy in his short youthful life.

"We uh hung out a lot, you know like what a couple would do, holding hands and hugging a little bit." Gary gulped as he prepared to lit what would no doubt be the final fuse. "And uh we mi-might have snogged just a little bit."

The gang took a deep breath and as if on cue, Leaf exploded, causing them all to cower in fear. "GARY OAK ARE YOU OUT OF YOUR MIND, WHAT WERE YOU THINKING, DRUGGING ME WITH LOVE POTION JUST TO GET ME TO GO OUT WITH YOU. FOR THE THREE HUNDRED AND SEVENTY FIFTH TIME, A NO MEANS A NO!"

"And you!" She continued, glaring daggers at the bunch of them huddled together far away from her bed, "What the hell were you guys thinking when you agreed to this stupid plan!"

The gang hung their head in shame, unable to face Leaf and she huffed angrily on her bed with her arms crossed. _Well at least the worst is over... right?_

xxx

"No." came the response, before Gary even opened his mouth.

"What! Come on, I haven even said anything yet!" Gary pleaded.

Leaf merely glared at him in a I-haven't-forgotten-what-you-did-to-me look, (which caused Gary to flinched badly), before stalking off without a backwards glance. Letting out a sigh, Gary made his way dejectedly to the rest of the gang as they sniggered a fair distance away, shaking their head at Gary's persistence and umpteenth failure.

"That would be the five hundred and thirteenth times he tried and failed," Paul commented, causing the gang to erupt in fresh peals of laughter at Gary's expense. Gary could only groan, cursing himself for listening to Ash back then, and for Leaf's stubbornness and small mindedness, who has not even begun to forgive him for the incident that took place years ago. Which is saying something because within the same period of time, Drew and May overcame their violent arguments, Dawn melted stone prince Paul's heart, and even someone as dense as Ash has figured out his feelings for Misty. Which also means that each one of Gary's friends are in a relationship even though he spent the longest time trying to woo a girl.

"You know, we still have the leftover Love Potions that would still work if they are administered properly." Ash piped up.

Gary only stared disbelieving at Ash's suggestion before proceeding to bang his head on a nearby wall. "Why do I have idiotic friends making my life so difficult ugh!"

* * *

 **A/N: Alright, hope you guys enjoyed this story! I tried to inject as much humour into the story as I could without making it sound too stupid. Was inspired by the thought of Love Potion, hence I set the story within the Harry Potter magical world. Hope you guys have a good laugh at Gary's failed attempts to get Leaf to go out with him! This is my first attempt at writing the characters from the Pokemon anime world, so I hope I captured them alright!**

 **I would love to hear what you think of this story, so please review and favourite if you liked this (:**


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